5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromide

HRID 2363724Notes

Reaction equation

HRID 2363724 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:17][N:16]=1>COCCOC>[BrH:1].[C:7]1([NH:6][C:4]([C:3]2[N:14]=[C:15]3[CH:20]=[CH:19][C:18]([B:21]4[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]4)=[CH:17][N:16]3[CH:2]=2)=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 132915193-Bromo-2-oxo-N-phenylpropanamide

Product 1

HCID 68778296N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromideYield 32.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1 g of 3-bromo-2-oxo-N-phenylpropionamide in 50 mL of 1,2-dimethoxyethane are added 1.09 g of 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. The reaction mixture is stirred for 40 hours at room temperature and then concentrated to dryness under reduced pressure. The residue is taken up in 30 mL of ethanol and refluxed for 90 minutes. After concentrating to dryness under reduced pressure, the solid is triturated in a small amount of ethanol, filtered off and washed with ethanol and then with ethyl ether to give 0.6 g of N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromide (1:1) in the form of a white solid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. temperaturerefluxed for 90 minutes
  3. concentrationAfter concentrating to dryness under reduced pressure
  4. customthe solid is triturated in a small amount of ethanol
  5. filtrationfiltered off
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-7686538c19814173b083cae5b5f5144f
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

Loading…